1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86596031, compound

HRID 747063Notes

Reaction equation

HRID 747063 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C@H:12]2[CH2:18][C:19](O)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S:22]1[CH2:27][CH2:26][CH2:25][S:24][CH:23]1[CH2:28][CH2:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38]C=1)[C@H:36](N)[CH2:35][CH2:34][CH2:33]2.C1C=CC2N(O)N=[N:47]C=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[S:24]1[CH2:25][CH2:26][CH2:27][S:22][CH:23]1[CH2:28][C:29]1[CH:38]=[C:37]2[C:32](=[CH:31][CH:30]=1)[C@H:33]([NH:47][C:19](=[O:20])[CH2:18][C@@H:12]1[C:13](=[O:17])[NH:14][CH2:15][CH2:16][N:11]1[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[CH2:34][CH2:35][CH2:36]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 33736660HCID 33736660, compoundHCID 86596032HCID 86596032, compound

Product 1

HCID 86596031HCID 86596031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-2-(1-(4-chlorophenylsulfonyl)-3-oxopiperazin-2-yl)acetic acid (1.98 g, 6.0 mmol), crude (R)-6-(2-(1,3-dithian-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-amine (1.8 g, 6.45 mmol), HOBt (892 mg, 6.6 mmol) and EDCI(1.265 g, 6.6 mmol)in 15 mL of DMF was stirred overnight at room temperature. After quenching with Sat. NaHCO3 solution, the reaction mixture was extracted with EtOAc/hexane (1:1, 200 mL×2). The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vaco. Flash chromatography (SiO2, hexane/EtOAc=2:1 to 3:2 to 1:1) gave the title compound as a white solid. MS: 609.7 (M+1).

Workup

  1. customAfter quenching with Sat. NaHCO3 solution
  2. extractionthe reaction mixture was extracted with EtOAc/hexane (1:1, 200 mL×2)
  3. washThe combined organic phase was washed brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vaco

Sources & evidence

ORD record
ord-13d9648759c9429fb6d985f602d32e61
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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